Formaldehyde → HCID 136005555, compound

HRID 1350389Notes

Reaction equation

HRID 1350389 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][NH:19][C@@H:18]([CH2:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:17]3)[C:4]=2[CH:3]=1.C=O.[CH2:32](Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][N:19]([CH3:32])[C@@H:18]([CH2:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:17]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 136005600HCID 136005600, compound

Product 1

HCID 136005555HCID 136005555, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Combine 2-methyl-10-((S)-3-(2-pyridin-3-yl-ethyl)-piperazin-1-yl)-4H-3-thia-4,9-diaza-benzo[f]azulene (728 mg, 1.80 mmol) and formaldehyde (158 μL, 1.98 mmol, 37% in water), and methylene chloride (30 mL). Stir 10 minutes at ambient temperature. Add sodium triacetoxyborohydride (573 mg, 2.70 mmol) and stir 1 hour at ambient temperature. Dilute with saturated sodium bicarbonate solution and extract with methylene chloride. Dry the extracts with sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (0%–4%) as the eluent to give the title compound (595 mg, 79%): Mass spectrum (ion spray): m/z=418 (M+1), 416 (M−1). Analysis calculated for C24H27N5S: C, 69.03; H, 6.52; N, 16.77. Found: C, 68.92; H, 6.60; N, 16.65.

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry the extracts with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate the filtrate
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-823a03af80124ad2b01813d960f83a1d
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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